good way of doing it, though with escorts getting a % of profits they will all want to guard the tankers rather than smaller ships (that can't be helped though). Would be more fun if you weren't zoner ided but just freelancer or had your own id as no-one pirates zoners (this is my experience when coming across pirates and zoners "you may pass zoner") so it would be boring for the escorts.
nice idea about new recruits having to fly hfs or lfs they'd be the first i've ever seen in space, everyone flys vhfs in my experience. would it be the same for the trader wing? i.e. Apprentice Transport Pilot limited to Armored Transport, or large transport, journeyman gets train or borderworlds etc